Literature DB >> 19301826

Inherent stereospecificity in the reaction of aflatoxin B(1) 8,9-epoxide with deoxyguanosine and efficiency of DNA catalysis.

Kyle L Brown1, Urban Bren, Michael P Stone, F Peter Guengerich.   

Abstract

Kinetic analysis of guanine alkylation by aflatoxin B(1) exo-8,9-epoxide, the reactive form of the hepatocarcinogen aflatoxin B(1), shows the reaction to be >2000 times more efficient in DNA than in aqueous solution, that is, with free 2'-deoxyguanosine. Thermodynamic analysis reveals AFB(1) exo-8,9-epoxide intercalation as the predominant source of the observed DNA catalytic effect. However, the known exo > endo epoxide stereospecificity of the DNA alkylation is observed even with free deoxyguanosine (ratio >20:1 determined by LC-MS and NMR measurements), as predicted by theoretical calculations [ Bren , U. , et al. ( 2007 ) Chem. Res. Toxciol. 20 , 1134 - 1140 ].

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Year:  2009        PMID： 19301826      PMCID： PMC3141577          DOI： 10.1021/tx900002g

Source DB:  PubMed          Journal:  Chem Res Toxicol        ISSN： 0893-228X            Impact factor:   3.739


  14 in total

1.  Direct detection and mapping of sites of base modification in DNA fragments by tandem mass spectrometry.

Authors:  Goutam Chowdhury; F Peter Guengerich
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Marked differences in base selectivity between DNA and the free nucleotides upon adduct formation from Bay- and Fjord-region diol epoxides.

Authors:  S R Vepachedu; N Ya; H Yagi; J M Sayer; D M Jerina
Journal:  Chem Res Toxicol       Date:  2000-09       Impact factor: 3.739

3.  Structural identification of the major DNA adduct formed by aflatoxin B1 in vitro.

Authors:  J M Essigmann; R G Croy; A M Nadzan; W F Busby; V N Reinhold; G Büchi; G N Wogan
Journal:  Proc Natl Acad Sci U S A       Date:  1977-05       Impact factor: 11.205

4.  WET, a T1- and B1-insensitive water-suppression method for in vivo localized 1H NMR spectroscopy.

Authors:  R J Ogg; P B Kingsley; J S Taylor
Journal:  J Magn Reson B       Date:  1994-05

5.  Intercalation of aflatoxin B1 in two oligodeoxynucleotide adducts: comparative 1H NMR analysis of d(ATCAFBGAT).d(ATCGAT) and d(ATAFBGCAT)2.

Authors:  S Gopalakrishnan; T M Harris; M P Stone
Journal:  Biochemistry       Date:  1990-11-20       Impact factor: 3.162

6.  Alteration of the aflatoxin cyclopentenone ring to a delta-lactone reduces intercalation with DNA and decreases formation of guanine N7 adducts by aflatoxin epoxides.

Authors:  K D Raney; S Gopalakrishnan; S Byrd; M P Stone; T M Harris
Journal:  Chem Res Toxicol       Date:  1990 May-Jun       Impact factor: 3.739

7.  Glutathione conjugation of aflatoxin B1 exo- and endo-epoxides by rat and human glutathione S-transferases.

Authors:  K D Raney; D J Meyer; B Ketterer; T M Harris; F P Guengerich
Journal:  Chem Res Toxicol       Date:  1992 Jul-Aug       Impact factor: 3.739

8.  DNA conformation mediates aflatoxin B1-DNA binding and the formation of guanine N7 adducts by aflatoxin B1 8,9-exo-epoxide.

Authors:  V M Raney; T M Harris; M P Stone
Journal:  Chem Res Toxicol       Date:  1993 Jan-Feb       Impact factor: 3.739

9.  Evidence for cytochrome P-450NF, the nifedipine oxidase, being the principal enzyme involved in the bioactivation of aflatoxins in human liver.

Authors:  T Shimada; F P Guengerich
Journal:  Proc Natl Acad Sci U S A       Date:  1989-01       Impact factor: 11.205

10.  Comparative binding and sequence interaction specificities of aflatoxin B1, aflatoxicol, aflatoxin M1, and aflatoxicol M1 with purified DNA.

Authors:  K Mariën; R Moyer; P Loveland; K Van Holde; G Bailey
Journal:  J Biol Chem       Date:  1987-06-05       Impact factor: 5.157
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  7 in total

1.  Carcinogenesis of urethane: simulation versus experiment.

Authors:  Andrej Lajovic; Leslie D Nagy; F Peter Guengerich; Urban Bren
Journal:  Chem Res Toxicol       Date:  2015-02-16       Impact factor: 3.739

2.  Effect of UV irradiation on aflatoxin reduction: a cytotoxicity evaluation study using human hepatoma cell line.

Authors:  Ankit Patras; Sharath Julakanti; Sudheer Yannam; Rishipal R Bansode; Mallory Burns; Matthew J Vergne
Journal:  Mycotoxin Res       Date:  2017-08-26       Impact factor: 3.833

3.  Retrospective and Prospective Look at Aflatoxin Research and Development from a Practical Standpoint.

Authors:  Noreddine Benkerroum
Journal:  Int J Environ Res Public Health       Date:  2019-09-27       Impact factor: 3.390

4.  Mutational spectra of aflatoxin B1 in vivo establish biomarkers of exposure for human hepatocellular carcinoma.

Authors:  Supawadee Chawanthayatham; Charles C Valentine; Bogdan I Fedeles; Edward J Fox; Lawrence A Loeb; Stuart S Levine; Stephen L Slocum; Gerald N Wogan; Robert G Croy; John M Essigmann
Journal:  Proc Natl Acad Sci U S A       Date:  2017-03-28       Impact factor: 11.205

5.  Prediction of potency of protease inhibitors using free energy simulations with polarizable quantum mechanics-based ligand charges and a hybrid water model.

Authors:  Debananda Das; Yasuhiro Koh; Yasushi Tojo; Arun K Ghosh; Hiroaki Mitsuya
Journal:  J Chem Inf Model       Date:  2009-12       Impact factor: 4.956

6.  Kinetics of DNA Adducts and Abasic Site Formation in Tissues of Mice Treated with a Nitrogen Mustard.

Authors:  Haoqing Chen; Ziyou Cui; Leila Hejazi; Lihua Yao; Scott J Walmsley; Carmelo J Rizzo; Robert J Turesky
Journal:  Chem Res Toxicol       Date:  2020-04-02       Impact factor: 3.739

7.  DNA Sequence Modulates Geometrical Isomerism of the trans-8,9- Dihydro-8-(2,6-diamino-4-oxo-3,4-dihydropyrimid-5-yl-formamido)- 9-hydroxy Aflatoxin B1 Adduct.

Authors:  Liang Li; Kyle L Brown; Ruidan Ma; Michael P Stone
Journal:  Chem Res Toxicol       Date:  2015-02-16       Impact factor: 3.739
  7 in total

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